Phenylboronic Acid → Ethyl 2-phenyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 917298ノート

反応式

HRID 917298 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2]

参加物

8

反応物 4

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 132827592-Bromo-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester

生成物 1

HCID 1483699Ethyl 2-phenyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate収率 60%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of thiazole III (2.0 g, 6.6 mmol) and the phenyl boronic acid (9.9 mmol) in THF (10 mL) was added potassium fluoride (1.15 g, 19.8 mmol), palladium (II) acetate (74 mg, 0.33 mmol), and 2-(di-t-butylphosphino)biphenyl (197 mg, 0.66 mmol). This mixture was stirred at 25° C. for 24 h. Diethyl ether (100 mL) was then added and the mixture was washed with 1 N aqueous NaOH (2×50 mL), saturated aqueous NaCl (1×50 mL), dried over MgSO4 and concentrated in vacuo to give an off-white solid. Purification by flash chromatography (silica, 0-2.5% ethyl acetate/hexane) gave the product, generally in 60-90% yield.

後処理

  1. washthe mixture was washed with 1 N aqueous NaOH (2×50 mL), saturated aqueous NaCl (1×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give an off-white solid
  5. customPurification by flash chromatography (silica, 0-2.5% ethyl acetate/hexane)
  6. customgave the product

出典と根拠

ORDレコード
ord-c71c4c60496a41b38418b116bdafcbe5
出典データセット
uspto-grants-2007_09
特許番号
US07273866B2

反応ノート

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